You may remember my friend Margaret from the Mighty Closet I did with her a few months ago. Ms. Stewart is one of my inspirations when I get dressed — she has a great eye and such a sense of fun — so when I took her photos, we did two sets. Here’s round two:

I covet this skirt. It’s so versatile and swishy.

When Margaret tried on this outfit, she wasn’t sure about the puffy Diane von Furstenberg shirt. She often pairs this skirt with a fitted black T-shirt. I felt like it depended on what she was going for; Margaret said she wasn’t sure she wanted to go for Eva Peron:

But come on. She rocks this.

The skirt is Marimekko for H&M, and it has me convinced that long skirts and T-shirts are the perfect San Francisco uniform. As User Experience Manager for You Tube, Margaret needs a lot of day to evening looks that don’t seem strange when the tech guys are still wearing sneakers at cocktail hour. Separates are the perfect option if you need to look presentable, but not overly fussy.

This antique ring is a tiny frog resting on a lilly pad. Margaret’s little girls are already fighting for ring rights.

Her versatile pointy-toe pumps are BP from Nordstrom. You may recognize them from my site banner.

The lacquer Bean Pendant is Elsa Peretti for Tiffany & Co. The hair is from God.

Do you have a moment to go all slack-jawed with me over M.Drummergirl’s keen fashion sense? (To clarify: I did not take these photos, they’re from her Flickr stream. M.Drummergirl and I have never met.)

She is a layering ninja.

And would you look at these colors? This is a girl after my own matchy-matchy heart.

Go marvel at the rest of her wardrobe trickery, all the more genius because so much of it is thrifted. And excuse me while I go home and iron.

If you’ve been reading long, you already know the drill from my packing posts about New York and Puerto Rico. I don’t like to check luggage if I can help it, so I try to fit everything in a carry-on and my laptop bag. This is what I packed for two weeks in Greece. It’s eight outfits total, and my plan was to wear everything twice, but on different islands.

This is my favorite vintage dress. It’s cotton and it has pockets, purrrr. Great for visiting churches when I’m traveling, because it covers the shoulders and knees, but it’s cool and easy to move in. I can also plop down on the ground without worrying I’m flashing everyone, so it’s good for traveling with the toddler too. The shoes are my navy saltwater sandals.

Because it’s cotton, this dress wrinkles in the suitcase, so Bryan taught me a trick from his acting days. Head into your hotel bathroom with the dress on a hanger, turn the shower on hot, wet a washcloth, wring it slightly, and then pat the dress down. The little wrinkles will fall out with the steam, and the wet washcloth takes care of the big ones. I just put the dress on damp and let it dry on me, but you can also let it dry overnight.

The glasses are a drugstore purchase from years ago, the headband is an elastic 99-center from H&M. So useful, that I actually gave Melissa one when we were in Puerto Rico, because she lamented having lost the ones she picked up in San Francisco. You need one too. More on that later.

This is a simple black, drop-waist dress that I got for $7 at a thrift store when I was in college. On the plane, I wore this with a pair of black leggings, my trusty slip-off gold flats (see Puerto Rico post if you’re curious about those), a pale blue cardigan, and my swimsuit wrap worn as a scarf (the wrap also doubled as a blanket). Again, I’ve failed you in photographing my travel outfit. Don’t think I can’t hear you cursing me from here.

I think the dress is rayon, but it reacts to water like crepe — either way, it doesn’t really wrinkle. I bought the hat for 10 Euros in Santorini, because I didn’t pack a sunhat. Which was dumb. Be ye not so dumb, my traveling friends.

The purse is from Buenos Aires, the necklace is my favorite, a gift from Bryan purchased at Rare Device. I can’t believe I’m blanking on the artist’s name. One of you knows, I’ll bet. Let me know in comments, and I’ll update.

These are the same shorts I took to Puerto Rico, they’re Rocawear. The shirt is a men’s undershirt, Hanes I think.

The brooch is a long vintage silk scarf that I made into a flower shape and pinned to my shirt with safety pins. Because I am crafty.

Oh man this dress is so good. Also vintage, and unfortunately polyester — the yucky kind. I got past it though, and it’s great for traveling.

Bryan brought back the bracelet from a work trip to China. All my cool jewelry is from Bryan.

The gladiator sandals were my main shoes for this trip. They’re surprisingly comfy, though buckled a little loose in this photo. They’re from Delia’s, which is a teen catalog that’s great for accessories and trendy stuff that you only need to last for a year or so.

Speaking of trendy stuff that doesn’t need to last, here’s a $15 romper I bought for the trip from Urban Outfitters (Be careful, that site now has music! Ugh).

I told you a while ago that I like to pack jammies that can double as outfits, and these were supposed to be my jammies. I ended up wearing them almost more than anything else, the knit was crazy comfortable. Action wear!

The giant earrings are from a shop in Kentucky. They’re lightweight.

Back to that headband. I keep it in my purse when I travel because my hair invariably starts to look scraggly with wind and swimming, or I get too hot to wear it down. With this, I can pull it into a ponytail and use the band to clean up the stray frizz caused by humidity. It’s easy to do without a mirror, and the result is casual, but a little more polished.

This dress is by 25singles. The sleeves are constructed so I can push them to the front and back and wear a cardigan without any added bulk on my shoulders. Great for the city.

Greece is all about jumping for me, apparently. Anyway, you can see here how the sleeves only attach at the top, so you can arrange the folds for more tummy or bum coverage, as you desire. Genius.

The necklace is actually two necklaces from H&M, which I knotted together.

Here are those shorts again. The tank is by H&M, and is much fuller than it appears in this photo. I actually decided it was a little unflattering on this trip, and probably won’t be wearing it again. Such are the perils of seeing yourself in photos.

The shoes were a blog rec by Elizabeth from Browner Brown. They’re $17 Saniya Pointed Toe Flats from Target, and they’re rubber soled. They didn’t give me problems on this trip, but have since given me pinky toe blisters. Great with tights though, and I love the color.

The scarf is the same one I used as a brooch above. This time I looped it twice around my head, tied it on top, and tucked the loose ends under for an updated Rosie the Riveter vibe.

This is another vintage find. That green band has crazy giraffes and other jungle animals in play, which is spectacular. Super comfy.

The fish-scale belt is elasticized, I got it at a thrift store. The waist on this dress is a little high for me, so I like to define it a bit.

Sunglasses were on loan from Laura, as an Englishman had accidentally absconded with mine the night before, thinking they were his girlfriend’s.

This is my swim wrap, which I bought in Bali on my honeymoon. It’s essentially a large rectangle of linen with a random button and a random tie. I have to figure out how to wear the damn thing every time I put it on, but it’s great to travel with because I can also use it as a scarf or a blanket on the plane. It’s by Oka Diputra.

The back gives you a little insight into how it’s fashioned. Button at the neck, tie at the waist. Supposedly you can wear it like fifteen different ways, but I have no idea how.

Here’s my new La Blanca suit! I’m excited because I almost never buy new swimsuits. I may just be turning over a new leaf on that though. (Sorry this is a little blown out, my camera was on the wrong setting.) I got it on sale at Nordstrom.com. I like that it’s a sexy one piece, but I don’t feel like my boobs are hanging out. Also? Red! Which is the very best color for a swimsuit.

And that’s it! Here’s a shot of my suitcase.

I had so much extra room, that I decided to throw in my rollers, which was ludicrous. I used them twice and they made my bag heavy, which is a Packing Light fail.

You can also sort of see that I packed two things that didn’t get much play, a yellow turban purchased in Puerto Rico, and a white men’s button down to wear as a coverup (I wore it for sleeping instead). The red and white striped thing is an adorable $10 beach bag from Walmart, which I used a couple times as a shopping bag, and to carry home Hank’s gifts without crushing them. I also had a pair of black flip-flops, which got a ton of use.

Regrets? Well, the stupid curlers. Come on, Maggie. Also, I should have worn a sunhat on the plane. It took a while to find a reasonable one, and I don’t totally love it. Also, in retrospect, I would have thrown in three or four more evening dresses. We tended to wear casual clothes during the day, and dress things up at night. It would have been good to have a few more in the vein of my 25singles dress.

Also, I would have stuffed my busy husband and my cranky toddler in, because as fun as it is to travel with girlfriends, I missed those guys.

I was in Greece because Intel is sponsoring my Mighty Life List. Next week, I’m going skin diving in the Arctic Circle! Stay tuned.

Courtney saw this BCBG Max Azaria pantsuit at Crossroads long before rompers came back in style. She couldn’t immediately figure out how to put it on, which she felt was a good sign. After some time wrangling in the dressing room, she decided to bring it home and figure it out.

Smart move, because it’s become Courtney’s version of the little black dress. That little diamond of exposed tummy skin is spot on. Courtney is smart about finding sexy clothes that don’t make her look too willing, if you know what I mean. She now thinks the jumper was an early sample, because she saw one at Nordstrom recently. She appears to be correct, because here it is. Did you pay $380 for yours, Skott? Yeah, I didn’t think so. High five.

The leafy earrings are Eliza Page, an Austin-based jeweler owned by a friend of Courtney’s. Lots of great stuff there, by the way.

This is Courtney just home from a long day of wit and wallpaper samples at Sugarbaker Designs. If you listen closely, you can just make out the opening strains of “Georgia on My Mind.” The red cuff is from Banana Republic.

The dress is Joanie Char Silk San Francisco, a score from the Goodwill. The details on this piece are lovely, including the line of shell buttons down the left hip.

When Courtney was in Spain, she visited this Desigual coat obsessively before finally splurging. Courtney has always been budget minded. We agreed during the shoot that spending $100 on something is a whole deal. If I’m spending more than $25 on an item, I tend to think it over. Thrift shopping makes you a crazy person that way. Lately I’ve begun to realize that it’s better to come home with one perfect investment piece rather than a garbage bag full of not-quite-there second hand stuff, so I’m trying to be better about looking for clothes that are bargains, but maybe not steals.

Courtney says the coat splurge was worth it, because people stop her on the street to compliment her whenever she wears it. I love that, because the whole point of going shopping while you travel is having the “Where’d you get that? conversation afterward. “This? Oh! I picked it up in Barcelona.”

These Cartonnier herringbone trousers from Anthropoligie are technically supposed to be “ankle length.” No hemming for the petite girl, hooray! This is a pretty typical work outfit for Courtney.

The Dolman-sleeved sweater is from Crossroads, a second-hand resale chain that has so far featured prominently in the Mighty Closet posts. I dig the proportions of this outfit. Easy, but not baggy, with a well-defined waist.

The necklace is from Crossroads too. Clearly we all need to spend more time at Crossroads.